Chlorotrimethylsilane → HCID 135903213、化合物

HRID 2191051ノート

反応式

HRID 2191051 の反応式
[NH2:1][C:2]1[NH:3][C:4](=[O:32])[C:5]2[N:6]=[CH:7][N:8]([C@@H:11]3[O:15][C@H:14]([CH2:16][CH:17]([P:26](=[O:29])([OH:28])[OH:27])S(C4C=CC=CC=4)=O)[C@@H:13]([F:30])[C@H:12]3[OH:31])[C:9]=2[N:10]=1.C(N(CCCC)CCCC)CCC.C[Si](Cl)(C)C>CN(C=O)C>[NH2:1][C:2]1[NH:3][C:4](=[O:32])[C:5]2[N:6]=[CH:7][N:8]([C@@H:11]3[O:15][C@H:14](/[CH:16]=[CH:17]/[P:26](=[O:27])([OH:29])[OH:28])[C@@H:13]([F:30])[C@H:12]3[OH:31])[C:9]=2[N:10]=1

参加物

5

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 7622TributylamineHCID 136351465HCID 136351465、化合物

生成物 1

HCID 135903213HCID 135903213、化合物収率 73.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

Compound 35.18 (12 mg, 0.025 mmol) was dissolved in anhydrous DMF (4 mL), treated with tributylamine (0.12 mL, 0.5 mmol) and TMSCl (0.063 mL, 0.5 mmol). The mixture was heated to 130° C. for 4 h, cooled to r.t., and then quenched with 2 mL water. The mixture was stirred at r.t for another 2 h and then the solvent was removed under reduced pressure. The residue was washed with 3×20 mL acetonitrile to remove TBA and TMSOH. The acetonitrile washes were discarded and the solid was dissolved in water, subjected to a reverse phase HPLC to give compound 35.19 (6.6 mg, 73% yield). 1HNMR (D2O, 300 MHz) δ 8.40 (s, 1H), 6.57 (m, 1H), 6.13 (t, 1H), 5.92 (d, 1H), 4.90-5.20(m, 3H). 31PNMR (D2O, 300 MHz): 11.815 ppm. LRMS (ESI) MH+ C11H13FN5O6P requires 362.1. Found 362.0.

後処理

  1. temperaturecooled to r.t.
  2. customquenched with 2 mL water
  3. customthe solvent was removed under reduced pressure
  4. washThe residue was washed with 3×20 mL acetonitrile
  5. customto remove TBA and TMSOH
  6. dissolutionthe solid was dissolved in water

出典と根拠

ORDレコード
ord-3637144873a04897a10bd924a1183a68
出典データセット
uspto-grants-2012_12
特許番号
US08324179B2

反応ノート

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